US4436743A - 3-[N-(Lower alkyl)-N-(tetrahydro-3-thienyl 5,5-dioxide)]sydnonimines - Google Patents
3-[N-(Lower alkyl)-N-(tetrahydro-3-thienyl 5,5-dioxide)]sydnonimines Download PDFInfo
- Publication number
- US4436743A US4436743A US06/350,366 US35036682A US4436743A US 4436743 A US4436743 A US 4436743A US 35036682 A US35036682 A US 35036682A US 4436743 A US4436743 A US 4436743A
- Authority
- US
- United States
- Prior art keywords
- compound according
- carbon atoms
- phenyl
- methyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Definitions
- the invention relates to pharmacologically active substituted 3-aminosydnonimines of the general formula I ##STR1## and their addition salts, wherein R 2 is --H or --CO--R 4 ;
- R 3 is methyl, ethyl, propyl or isopropyl
- R 4 is aliphatic hydrocarbyl with from 1 to 4 carbon atoms and optionally substituted by alkoxy with from 1 to 3 carbon atoms, cycloaliphatic hydrocarbyl with from 5 to 7 ring carbon atoms, bicycloaliphatic hydrocarbyl with from 7 to 14 ring carbon atoms, tricycloaliphatic hydrocarbyl with from 7 to 16 ring carbon atoms, alkoxy with from 1 to 6 carbon atoms, carbocyclic aryloxy with from 6 to 12 ring carbon atoms, alkoxycarbonyl with from 2 to 7 carbon atoms, carbocyclic aryl with from 6 to 12 ring carbon atoms or such aryl with from 1 to 3 substituents each of which is a member selected from the group consisting of halo, alkyl with from 1 to 3 carbon atoms, alkoxy with from 1 to 3 carbon atoms and nitro, and at most 2 of which are nitro; and
- n is a positive whole number of at most 2.
- the invention furthermore relates to a process for the preparation of the compounds according to the invention and to their use.
- Aliphatic radicals, alkoxy radicals or alkoxycarbonyl radicals R 4 can be straight-chain or branched. Possible aliphatic radicals R 4 are, in particular, alkyl radicals with 1 to 4 C atoms. The methoxymethyl radical may be mentioned, in particular, as an aliphatic radical R 4 which is substituted by alkoxy with 1 to 3 C atoms. Possible cycloaliphatic radicals R 4 are, above all, cycloalkyl radicals with 5 to 7 C atoms, in particular cyclopentyl and, preferably, cyclohexyl.
- Possible alkoxy radicals R 4 are, in particular, the methoxy and ethoxy radicals.
- a possible alkoxycarbonyl radical R 4 is, in particular, the ethoxycarbonyl radical.
- Aryl radicals R 4 which may be mentioned are, for example, ⁇ - or ⁇ -naphthyl radicals, but in particular the phenyl radical.
- Aryloxy radicals R 4 which may be mentioned are, for example, ⁇ - or ⁇ -naphthoxy radicals, but in particular the phenoxy radical.
- the aryl radicals R 4 can be monosubstituted, disubstituted or trisubstituted, but even in the case of trisubstitution, only at most 2 nitro groups may be present, such as, for example, 2-methyl-4,6-dinitrophenyl and 2-chloro-6-methyl-4-nitrophenyl.
- Possible halogen substituents for the aryl radicals are, for example, chlorine and bromine atoms.
- Substituted aryl radicals R 4 which may be mentioned are, in particular: methyl-phenyl (tolyl), nitro-phenyl and chloro-phenyl.
- R 3 is preferably methyl or ethyl.
- R 4 is preferably methyl, ethyl, cyclohexyl, phenyl, 4-chloro-phenyl or 4-nitrophenyl.
- Cyclisation of the compounds II to give the compounds Ia is carried out in a suitable organic or inorganic solvent, for example water, an alkanol with 1 to 4 C atoms, a carboxylic acid alkyl ester, for example ethyl acetate, or a mixture of such solvents, such as water/methanol or, preferably, ethyl acetate/methanol, with the addition of a cyclising agent, usually at temperatures from 0° to 40° C., preferably at 0° to 20° C.
- a suitable organic or inorganic solvent for example water, an alkanol with 1 to 4 C atoms, a carboxylic acid alkyl ester, for example ethyl acetate, or a mixture of such solvents, such as water/methanol or, preferably, ethyl acetate/methanol
- Suitable cyclising agents are those which establish a pH value below 3 in aqueous solution, thus, for example, mineral acids, such as sulphuric acid, nitric acid, phosphoric acid or, preferably, hydrochloric acid, and also strong organic acids, such as trifluoroacetic acid.
- the cyclisation gives the corresponding acid addition salt of the compound Ia.
- the compounds of formula Ia are compounds according to the invention where R 2 is hydrogen.
- the acylation is carried out in a suitable solvent, such as, for example, water, a polar organic solvent, such as dimethylformamide, dimethylsulphoxide or pyridine, a solvent mixture, such as, for example, water/methylene chloride, or in an excess of the acylating agent, advantageously whilst stirring and at temperatures from 0° C. to the boiling point of the solvent or acylating agent, preferably from 0° to 20° C.
- An acid-binding agent such as, for example, pyridine, sodium bicarbonate or sodium acetate, is advantageously present during the acylation.
- the substituted 3-amino-sydnonimines of the general formula I form acid addition salts with inorganic or organic acids.
- Inorganic and organic acids are suitable for the formation of such acid addition salts.
- suitable acids are hydrogen chloride, hydrogen bromide, naphthalenedisulphonic acids, in particular naphthalene-1,5-disulphonic acid, and phosphoric, nitric, sulphuric, oxalic, lactic, tartaric, acetic, salicylic, benzoic, formic, propionic, pivalic, diethylacetic, malonic, succinic, pimelic, fumaric, maleic, malic, sulphamic, phenylpropionic, gluconic, ascorbic, isonicotinic, methanesulphonic, p-toluenesulphonic, citric or adipic acid.
- the acid addition salts can be prepared in the customary manner by combining the components, advantageously in a suitable solvent or diluent. In the synthesis of compounds of the formula Ia, the acid addition salts are obtained. If desired, the free compounds of the general formula I or Ia can be obtained from the acid addition salts in a known manner, that is to say by dissolving or suspending the salts in water, rendering the solution or suspension alkaline, for example with sodium hydroxide solution, and then isolating the free compounds.
- All acid-addition salts are within the scope of this invention. Those which are pharmacologically acceptable are directly useful as hereinafter taught. Those which are not pharmacologically acceptable are readily converted by known and well-established conventional procedures either to their corresponding free bases or to pharmacologically-acceptable acid-addition salts. All pharmacologically-acceptable acid-addition salts of the pharmacologically-active substituted 3-aminosydnonimines of formula I are useful for treating or preventing cardiovascular system disorders, such as high blood pressure and angina pectoris.
- the starting compounds of the general formula II required can be prepared in a manner which is in itself known by Strecker aminonitrile synthesis from compounds of the general formula IV
- the nitrosation is carried out in a known manner in a suitable solvent, preferably in water, at temperatures from 0° to 10° C.
- the nitrous acid is usually produced from an alkali metal nitrite and hydrochloric acid. It is advantageous to adjust the aqueous solution of the compound V to a pH value of 1 to 3 with hydrochloric acid and to add an aqueous solution of the alkali metal nitrite dropwise to the stirred and cooled solution of the compound.
- the solution of the resulting compound II can be subjected directly to the cyclisation reaction. However, it is usually appropriate first to take up the nitroso compound II in a suitable organic solvent and to carry out the cyclisation to give the compound of the formula I in this solvent, if appropriate after adding a further solvent.
- the compounds of the formula I and their pharmacologically acceptable acid addition salts can therefore be administered to humans as drugs by themselves, as mixtures with one another or in the form of pharmaceutical formulations which permit enteral or parenteral administration and contain, as the active constituent, an effective dose of at least one compound of the formula I or of an acid addition salt thereof, in addition to customary pharmaceutically acceptable excipients and additives.
- the drugs can be administered orally, for example in the form of pills, tablets, coated tablets, dragees, hard and soft gelatine capsules, solutions, syrups, emulsions or suspensions, or as aerosol mixtures. Administration can, however, also be effected rectally, for example in the form of suppositories, parenterally, for example in the form of injection solutions, or percutaneously, for example in the form of ointments or tinctures.
- Pills, tablets, dragees and hard gelatine capsules can be prepared using, for example, lactose, maize starch or derivatives thereof, talc, stearic acid or salts thereof, and the like.
- excipients for soft gelatine capsules and suppositories are fats, waxes, semi-solid and liquid polyols, natural or hardened oils and the like.
- suitable excipients for the preparation of solutions and syrups are water, sucrose, invert sugar, glucose, polyols and the like.
- suitable excipients for the preparation of injection solutions are water, alcohols, glycerol, polyols, vegetable oils and the like.
- the pharmaceutical products can also contain additives, such as, for example, fillers, extenders, disintegrating agents, binders, lubricants, wetting agents, stabilisers, emulsifiers, preservatives, sweeteners, colorants, flavouring or aromatising agents, thickeners, diluents and buffer substances, and also solvents or solubilising agents or agents for achieving a depot effect, as well as salts for modifying the osmotic pressure, coating agents or antioxidants.
- additives such as, for example, fillers, extenders, disintegrating agents, binders, lubricants, wetting agents, stabilisers, emulsifiers, preservatives, sweeteners, colorants, flavouring or aromatising agents, thickeners, diluents and buffer substances, and also solvents or solubilising agents or agents for achieving a depot effect, as well as salts for modifying the osmotic pressure, coating agents or antioxidants.
- They can also contain two or more
- ⁇ -blockers such as, for example, propranolol, pindolol and metoprolol
- vasodilators such as, for example, carbochromene
- tranquillisers such as, for example, barbituric acid derivatives, 1,4-benzodiazepines and meprobamate
- diuretics such as, for example, chlorothiazide
- cardiac tonics such as, for example, digitalis products
- hypotensive agents such as, for example, hydralazine, dihydralazine, prazosin, clonidine and Rauwolfia alkaloids
- agents which reduce the level of fatty acids in the blood such as, for example, bezafibrate and fenofibrate
- agents for the prophylaxis of thromboses such as, for example, phenprocoumon.
- the compounds of the formula I, their pharmacologically acceptable acid addition salts and pharmaceutical products which contain the compounds of the formula I or their pharmacologically acceptable acid addition salts as active compounds can be used on humans for combating or preventing illnesses of the cardiovascular system, for example as antihypertensive drugs for various forms of high blood pressure, for combating or preventing angina pectoris, and the like.
- the dosage can vary within wide limits and is to be adapted to the individual circumstances in each separate case.
- a daily dose of about 0.5 to 100 mg, preferably 1 to 20 mg, per person is appropriate in the case of oral administration. Because of the good absorption of the active compounds, the daily dose for other forms of administration is also within a similar range, that is to say in general also 0.5 to 100 mg/person.
- the daily dose is usually divided into several, for example 2 to 4, part administrations.
- the animals under urethane/chloralose anaesthesia received no continuous infusion.
- the infusion was effected through the cephalic vein. After preparation of the experimental animals, a period of about 1 hour was allowed for all the haemodynamic parameters to become established (steady state). The actual experiment was then started.
- BP mean peripheral blood pressure
- systolic and diastolic blood pressure were measured peripherally in the femoral artery via a Statham pressure recorder.
- the percentage data are by weight.
- Decomp. denotes decomposition.
- the cyclisation proceeds in a similar manner if sulphuric acid, nitric acid, phosphoric acid or trifluoroacetic acid is used instead of hydrogen chloride, and/or if the cyclisation is carried out at temperatures from 0° to 40° C., and/or if the methanol is replaced by a corresponding amount of ethyl acetate, ethanol, i-propanol, n-propanol, i-butanol or n-butanol.
- the cyclisation proceeds in a similar manner if sulphuric acid, nitric acid, phosphoric acid or trifluoroacetic acid is used instead of hydrogen chloride and/or the cyclisation is carried out at temperatures from 0° to 40° C., and/or the methanol is replaced by a corresponding amount of ethyl acetate, ethanol, i-propanol, n-propanol, i-butanol or n-butanol.
- Tablets containing 2 mg of active compound per tablet Tablets containing 2 mg of active compound per tablet:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Furan Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pyrane Compounds (AREA)
- Seasonings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19813107933 DE3107933A1 (de) | 1981-03-02 | 1981-03-02 | Substituierte 3-amino-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung |
DE3107933 | 1981-03-02 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/477,146 Division US4551454A (en) | 1981-03-02 | 1983-05-06 | 3-(4-Alkoxycarbonylpiperazin-1-yl)-sydnonimines, a process for their preparation and use |
Publications (1)
Publication Number | Publication Date |
---|---|
US4436743A true US4436743A (en) | 1984-03-13 |
Family
ID=6126174
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/350,366 Expired - Fee Related US4436743A (en) | 1981-03-02 | 1982-02-19 | 3-[N-(Lower alkyl)-N-(tetrahydro-3-thienyl 5,5-dioxide)]sydnonimines |
US06/477,146 Expired - Fee Related US4551454A (en) | 1981-03-02 | 1983-05-06 | 3-(4-Alkoxycarbonylpiperazin-1-yl)-sydnonimines, a process for their preparation and use |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/477,146 Expired - Fee Related US4551454A (en) | 1981-03-02 | 1983-05-06 | 3-(4-Alkoxycarbonylpiperazin-1-yl)-sydnonimines, a process for their preparation and use |
Country Status (23)
Country | Link |
---|---|
US (2) | US4436743A (de) |
EP (1) | EP0059356B1 (de) |
JP (1) | JPS57158768A (de) |
KR (1) | KR880001428B1 (de) |
AT (1) | ATE13055T1 (de) |
AU (1) | AU545292B2 (de) |
CA (1) | CA1192905A (de) |
CS (1) | CS224645B2 (de) |
DD (1) | DD208617A5 (de) |
DE (2) | DE3107933A1 (de) |
DK (1) | DK149852C (de) |
ES (1) | ES510015A0 (de) |
FI (1) | FI820518L (de) |
HU (1) | HU190683B (de) |
IL (1) | IL65141A (de) |
NO (1) | NO820476L (de) |
NZ (1) | NZ199862A (de) |
PH (1) | PH18696A (de) |
PL (1) | PL136818B1 (de) |
PT (1) | PT74507B (de) |
RO (1) | RO84816B (de) |
SU (1) | SU1097197A3 (de) |
ZA (1) | ZA821327B (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4551454A (en) * | 1981-03-02 | 1985-11-05 | Cassella Aktiengesellschaft | 3-(4-Alkoxycarbonylpiperazin-1-yl)-sydnonimines, a process for their preparation and use |
US4845091A (en) * | 1985-07-20 | 1989-07-04 | Cassella Aktiengesellschaft | Substituted 3-amino-sydnonimines, their use and pharmaceutical products containing them |
US4895726A (en) * | 1988-02-26 | 1990-01-23 | Fournier Innovation Et Synergie | Novel dosage form of fenofibrate |
US4937244A (en) * | 1987-09-24 | 1990-06-26 | Cassella Aktiengesellschaft | Substituted 3-aminosydnonimines, processes for their preparation and their use |
US5120732A (en) * | 1988-06-14 | 1992-06-09 | Cassella Aktiengesellschaft | Substituted 3-aminosyndone imines, a process for their preparation and their use |
US5155109A (en) * | 1990-10-04 | 1992-10-13 | Cassella Aktiengesellschaft | 3-piperazinosydnone imines, process for their preparation and their use |
US20020009496A1 (en) * | 1997-01-17 | 2002-01-24 | Andre Stamm | Fenofibrate pharmaceutical composition having high bioavailability and method for preparing it |
US6531158B1 (en) | 2000-08-09 | 2003-03-11 | Impax Laboratories, Inc. | Drug delivery system for enhanced bioavailability of hydrophobic active ingredients |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5859977A (ja) * | 1981-10-06 | 1983-04-09 | Banyu Pharmaceut Co Ltd | 新規なn−アシルシドノンイミン誘導体およびその製法 |
US4517179A (en) * | 1983-04-29 | 1985-05-14 | Pennwalt Corporation | Rapid dissolving, uniform drug compositions and their preparation |
DK243084A (da) * | 1983-05-26 | 1984-11-27 | Takeda Chemical Industries Ltd | Perkutane farmaceutiske praeparater til udvortes brug |
DE3702083A1 (de) * | 1987-01-24 | 1988-08-04 | Cassella Ag | Allylmercaptoacetyl-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung |
US5221680A (en) * | 1988-01-14 | 1993-06-22 | Cassella Aktiengesellschaft | Substituted 3-aminosydnonimines |
DE4025604A1 (de) * | 1990-08-13 | 1992-02-20 | Cassella Ag | 3-dicyclohexylamino-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung |
DE4028679A1 (de) * | 1990-09-10 | 1992-03-19 | Cassella Ag | Substituierte 3-aminosydnonimine, verfahren zu ihrer herstellung und ihre verwendung |
WO1997017334A1 (fr) * | 1995-11-06 | 1997-05-15 | Chugai Seiyaku Kabushiki Kaisha | Derives d'imine de sydnone |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3769283A (en) | 1966-07-04 | 1973-10-30 | Takeda Chemical Industries Ltd | N-acyl sydnonimine derivatives |
US3833580A (en) | 1966-08-09 | 1974-09-03 | Boehringer Sohn Ingelheim | 3-morpholino-n6-cyclohexylcarbonyl sydnonimine |
US3833589A (en) | 1972-07-31 | 1974-09-03 | Sandoz Ag | Substituted sydnonimine nitrate esters |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE788052A (fr) * | 1971-08-26 | 1973-02-26 | Science Union & Cie Societe Fr | Nouveaux derives de la sydnone imine |
DE2930736A1 (de) * | 1979-07-28 | 1981-02-12 | Cassella Ag | Pharmakologisch wirksame, substituierte 3-amino-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung |
DE3107933A1 (de) * | 1981-03-02 | 1982-09-16 | Cassella Ag, 6000 Frankfurt | Substituierte 3-amino-sydnonimine, verfahren zu ihrer herstellung und ihre verwendung |
JPS5832870A (ja) * | 1981-08-24 | 1983-02-25 | Hiroyoshi Hidaka | 新規なシドノンイミン誘導体及びその製法 |
JPS5859977A (ja) * | 1981-10-06 | 1983-04-09 | Banyu Pharmaceut Co Ltd | 新規なn−アシルシドノンイミン誘導体およびその製法 |
-
1981
- 1981-03-02 DE DE19813107933 patent/DE3107933A1/de not_active Withdrawn
-
1982
- 1982-02-15 DE DE8282101091T patent/DE3263342D1/de not_active Expired
- 1982-02-15 AT AT82101091T patent/ATE13055T1/de not_active IP Right Cessation
- 1982-02-15 EP EP82101091A patent/EP0059356B1/de not_active Expired
- 1982-02-16 FI FI820518A patent/FI820518L/fi not_active Application Discontinuation
- 1982-02-16 DK DK67682A patent/DK149852C/da not_active IP Right Cessation
- 1982-02-16 NO NO820476A patent/NO820476L/no unknown
- 1982-02-19 US US06/350,366 patent/US4436743A/en not_active Expired - Fee Related
- 1982-02-26 RO RO106750A patent/RO84816B/ro unknown
- 1982-02-26 CA CA000397186A patent/CA1192905A/en not_active Expired
- 1982-02-26 DD DD82237741A patent/DD208617A5/de unknown
- 1982-03-01 HU HU82616A patent/HU190683B/hu unknown
- 1982-03-01 AU AU80966/82A patent/AU545292B2/en not_active Ceased
- 1982-03-01 ES ES510015A patent/ES510015A0/es active Granted
- 1982-03-01 ZA ZA821327A patent/ZA821327B/xx unknown
- 1982-03-01 NZ NZ199862A patent/NZ199862A/en unknown
- 1982-03-01 PH PH26931A patent/PH18696A/en unknown
- 1982-03-01 JP JP57030669A patent/JPS57158768A/ja active Pending
- 1982-03-01 IL IL65141A patent/IL65141A/xx unknown
- 1982-03-01 SU SU823398796A patent/SU1097197A3/ru active
- 1982-03-01 PL PL1982235274A patent/PL136818B1/pl unknown
- 1982-03-01 PT PT74507A patent/PT74507B/de unknown
- 1982-03-02 CS CS821412A patent/CS224645B2/cs unknown
- 1982-03-02 KR KR8200898A patent/KR880001428B1/ko active
-
1983
- 1983-05-06 US US06/477,146 patent/US4551454A/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3769283A (en) | 1966-07-04 | 1973-10-30 | Takeda Chemical Industries Ltd | N-acyl sydnonimine derivatives |
US3833580A (en) | 1966-08-09 | 1974-09-03 | Boehringer Sohn Ingelheim | 3-morpholino-n6-cyclohexylcarbonyl sydnonimine |
US3833589A (en) | 1972-07-31 | 1974-09-03 | Sandoz Ag | Substituted sydnonimine nitrate esters |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4551454A (en) * | 1981-03-02 | 1985-11-05 | Cassella Aktiengesellschaft | 3-(4-Alkoxycarbonylpiperazin-1-yl)-sydnonimines, a process for their preparation and use |
US4845091A (en) * | 1985-07-20 | 1989-07-04 | Cassella Aktiengesellschaft | Substituted 3-amino-sydnonimines, their use and pharmaceutical products containing them |
US4937244A (en) * | 1987-09-24 | 1990-06-26 | Cassella Aktiengesellschaft | Substituted 3-aminosydnonimines, processes for their preparation and their use |
US4895726A (en) * | 1988-02-26 | 1990-01-23 | Fournier Innovation Et Synergie | Novel dosage form of fenofibrate |
US5120732A (en) * | 1988-06-14 | 1992-06-09 | Cassella Aktiengesellschaft | Substituted 3-aminosyndone imines, a process for their preparation and their use |
US5155109A (en) * | 1990-10-04 | 1992-10-13 | Cassella Aktiengesellschaft | 3-piperazinosydnone imines, process for their preparation and their use |
US20020009496A1 (en) * | 1997-01-17 | 2002-01-24 | Andre Stamm | Fenofibrate pharmaceutical composition having high bioavailability and method for preparing it |
US20030104060A1 (en) * | 1997-01-17 | 2003-06-05 | Andre Stamm | Fenofibrate pharmaceutical composition having high bioavailability |
US20090035379A1 (en) * | 1997-01-17 | 2009-02-05 | Cabinet Hirsch | Fenofibrate compositions |
US8329214B2 (en) | 1997-01-17 | 2012-12-11 | Laboratoires Fournier S.A. | Process for producing fenofibrate tablets |
US8343540B2 (en) | 1997-01-17 | 2013-01-01 | Laboratories Fournier S.A. | Process for producing fenofibrate tablets |
US6531158B1 (en) | 2000-08-09 | 2003-03-11 | Impax Laboratories, Inc. | Drug delivery system for enhanced bioavailability of hydrophobic active ingredients |
Also Published As
Publication number | Publication date |
---|---|
PH18696A (en) | 1985-09-05 |
RO84816A (ro) | 1984-08-17 |
HU190683B (en) | 1986-10-28 |
ES8303404A1 (es) | 1983-02-01 |
DE3263342D1 (en) | 1985-06-05 |
CS224645B2 (en) | 1984-01-16 |
DE3107933A1 (de) | 1982-09-16 |
RO84816B (ro) | 1984-09-30 |
DD208617A5 (de) | 1984-04-04 |
ES510015A0 (es) | 1983-02-01 |
EP0059356B1 (de) | 1985-05-02 |
NZ199862A (en) | 1985-04-30 |
IL65141A0 (en) | 1982-05-31 |
KR880001428B1 (ko) | 1988-08-08 |
KR830009062A (ko) | 1983-12-17 |
FI820518L (fi) | 1982-09-03 |
DK149852B (da) | 1986-10-13 |
PT74507A (de) | 1982-04-01 |
DK149852C (da) | 1987-06-01 |
NO820476L (no) | 1982-09-03 |
AU545292B2 (en) | 1985-07-11 |
ATE13055T1 (de) | 1985-05-15 |
AU8096682A (en) | 1982-09-16 |
US4551454A (en) | 1985-11-05 |
PL136818B1 (en) | 1986-03-31 |
CA1192905A (en) | 1985-09-03 |
PT74507B (de) | 1983-11-08 |
ZA821327B (en) | 1983-01-26 |
IL65141A (en) | 1984-10-31 |
DK67682A (da) | 1982-09-03 |
EP0059356A1 (de) | 1982-09-08 |
JPS57158768A (en) | 1982-09-30 |
SU1097197A3 (ru) | 1984-06-07 |
PL235274A1 (de) | 1982-10-25 |
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